The concept of the “new Cold War” has featured prominently in recent debates about the present and future of U.S.-China relations. Meanwhile, tensions in the Taiwan Strait have sparked considerable debate on the United States’ relationship with Taiwan. There have not, however, been efforts to integrate these two debates to consider whether or not the Cold War analogy applies to great power competition in the Taiwan Strait. This paper analyzes the dispute over Taiwan in the Cold War era and the present day, highlighting both similarities and differences. Despite the vast changes in ideology and regime type in Taiwan, important aspects of this issue have remained consistent since 1949. Continuities include Taiwan’s concern about abandonment; the United States’ concern about entrapment; the United States’ neutral position on Taiwan’s sovereignty; the United States and Taiwan both positioning Taiwan as the ideological alternative to the PRC; and Beijing spuriously claiming that it has the support of Taiwan’s people. Discontinuities also exist, including Taiwan’s transition to a liberal democracy; changing national identity among the electorate; the decline in support for One-China; Taiwan’s higher political importance for Beijing; the distribution of capabilities in the Taiwan Strait; economic interdependence between the United States, China, and Taiwan; and Taiwan’s geoeconomic importance. Based on a comparison of these continuities and discontinuities, this article argues that the risk of conflict in the Taiwan Strait is greater now than it was during the Cold War.